WO2021235549A1 - Composé, matériau électroluminescent et élément électroluminescent - Google Patents

Composé, matériau électroluminescent et élément électroluminescent Download PDF

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WO2021235549A1
WO2021235549A1 PCT/JP2021/019431 JP2021019431W WO2021235549A1 WO 2021235549 A1 WO2021235549 A1 WO 2021235549A1 JP 2021019431 W JP2021019431 W JP 2021019431W WO 2021235549 A1 WO2021235549 A1 WO 2021235549A1
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group
substituted
light emitting
carbazole
ring
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Japanese (ja)
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正貴 山下
碩賢 鄭
ウママヘシュ バリジャパリ
ユソク ヤン
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株式会社Kyulux
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Priority to US17/999,440 priority Critical patent/US20230210000A1/en
Priority to KR1020227041579A priority patent/KR20230015360A/ko
Priority to EP21808197.4A priority patent/EP4155309A4/fr
Priority to CN202180036659.0A priority patent/CN115698016A/zh
Publication of WO2021235549A1 publication Critical patent/WO2021235549A1/fr

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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
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    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound useful as a light emitting material and a light emitting device using the compound.
  • organic electroluminescence elements organic electroluminescence elements
  • various measures have been taken to improve the luminous efficiency by newly developing and combining electron transport materials, hole transport materials, light emitting materials and the like constituting organic electroluminescence devices.
  • research on organic electroluminescence devices using delayed fluorescent materials can be seen.
  • the delayed fluorescent material is a material that emits fluorescence when returning from the excited singlet state to the ground state after an intersystem crossing from the excited triplet state to the excited singlet state occurs in the excited state. Fluorescence by such a pathway is called delayed fluorescence because it is observed later than the fluorescence from the excited singlet state directly generated from the ground state (normal fluorescence).
  • the probability of occurrence of the excited singlet state and the excited triplet state is statistically 25%: 75%, so that the excited singlet state directly generated is used. There is a limit to the improvement of light emission efficiency only by the fluorescence of.
  • the delayed fluorescent material not only the excited singlet state but also the excited triplet state can be used for fluorescence emission by the path via the above-mentioned inverse intersystem crossing, so that the emission is higher than that of the ordinary fluorescent material. Efficiency will be obtained.
  • any material that emits delayed fluorescence is not immediately useful as a light emitting material.
  • Some delayed fluorescent materials are relatively unlikely to have an inverse intersystem crossing, and some have a long delayed fluorescence lifetime.
  • excitons may accumulate in the high current density region to reduce the luminous efficiency, or the drive may deteriorate rapidly if the drive is continued for a long time. Therefore, the reality is that there are an extremely large number of delayed fluorescent materials that have room for improvement in terms of practicality. Therefore, it has been pointed out that the benzonitrile compound known as a delayed fluorescent material also has a problem.
  • a compound having the following structure is a material that emits delayed fluorescence (see Patent Document 1), it has problems that the delayed fluorescence has a long life and the device durability is insufficient.
  • the present inventors have conducted repeated studies for the purpose of providing a more useful compound as a light emitting material for a light emitting device. Then, we proceeded with diligent studies for the purpose of deriving and generalizing the general formulas of compounds that are more useful as luminescent materials.
  • the present inventors have found that among the isophthalonitrile derivatives, a compound having a structure satisfying a specific condition is useful as a light emitting material.
  • the present invention has been proposed based on these findings, and specifically has the following configurations.
  • R is a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded at a carbon atom.
  • Ar is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded at a carbon atom.
  • D 1 and D 2 each independently represent a donor group, of which at least one is a heterocyclic condensed carbazole-9-yl group (the heterocycle and the carbazole may be substituted).
  • the thiophene ring and the pyrrole ring may be further fused with another ring), and two heterocycles selected from the group are condensed, any one of [1] to [9].
  • [17] The compound according to any one of [1] to [16], which comprises an atom selected from the group consisting of a carbon atom, a hydrogen atom, a heavy hydrogen atom, a nitrogen atom, an oxygen atom and a sulfur atom.
  • a luminescent material comprising the compound according to any one of [1] to [17].
  • a light emitting device comprising the compound according to any one of [1] to [17].
  • the light emitting device according to [20] wherein the light emitting device has a light emitting layer, the light emitting layer contains the compound and the light emitting material, and mainly emits light from the light emitting material.
  • the compound of the present invention is useful as a light emitting material. Further, the compound of the present invention includes a compound having a short delayed fluorescence lifetime. Further, the organic light emitting device using the compound of the present invention has high device durability and is useful.
  • the description of the constituent elements described below may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples.
  • the numerical range represented by using "-" in the present specification means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
  • part or all of the hydrogen atoms present in the molecule of the compound used in the present invention can be replaced by deuterium atoms (2 H, deuterium D).
  • the hydrogen atom is indicated as H or the indication is omitted.
  • At least one of D 1 and D 2 in the general formula (1) represents a heterocyclic condensed carbazole-9-yl group.
  • the heterocycle and the carbazole ring constituting the heterocyclic condensed carbazole-9-yl group may or may not be substituted, respectively.
  • the number of heterocycles fused to the carbazole-9-yl group is one or more, preferably one or two, and more preferably one. When two or more heterocycles are fused, they may be the same or different.
  • the heterocycle is condensed at positions 1 and 2 of the carbazole-9-yl group.
  • the heterocycle is condensed to the 2nd and 3rd positions of the carbazole-9-yl group.
  • the heterocycle is fused to the 3rd and 4th positions of the carbazole-9-yl group.
  • the heterocycle condensed on the carbazole-9-yl group is a ring containing a heteroatom.
  • the heteroatom is preferably selected from an oxygen atom, a sulfur atom, a nitrogen atom and a silicon atom, and more preferably selected from an oxygen atom, a sulfur atom and a nitrogen atom.
  • the heteroatom is an oxygen atom.
  • the heteroatom is a sulfur atom.
  • the heteroatom is a nitrogen atom.
  • the number of heteroatoms contained as ring skeleton constituent atoms of the heterocycle is one or more, preferably 1 to 3, and more preferably 1 or 2. In one preferred embodiment, the number of heteroatoms is one. When the number of heteroatoms is two or more, they are preferably heteroatoms of the same type, but may be composed of heteroatoms of different types. For example, two or more heteroatoms may all be nitrogen atoms. Ring skeleton constituent atoms other than heteroatoms are carbon atoms. The number of ring skeleton constituent atoms constituting the heterocycle condensed with the carbazole-9-yl group is preferably 4 to 8, more preferably 5 to 7, and further preferably 5 or 6. preferable.
  • the number of ring skeleton constituent atoms constituting the heterocycle is 5. It is preferable that two or more conjugated double bonds are present in the heterocycle, and it is preferable that the conjugated system of the carbazole ring is expanded by condensing the heterocycle (having aromaticity). preferable).
  • Preferred examples of the heterocycle include a furan ring, a thiophene ring, and a pyrrole ring. Further, another ring may be condensed on the heterocycle condensed on the carbazole-9-yl group. Further, the ring to be condensed may be a monocyclic ring or a condensed ring.
  • Examples of the ring to be condensed include an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle.
  • Examples of the aromatic hydrocarbon ring include a benzene ring.
  • Examples of the aromatic heterocycle include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a pyrrole ring, a pyrazole ring, and an imidazole ring.
  • Examples of the aliphatic hydrocarbon ring include a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring.
  • Examples of the aliphatic heterocycle include a piperidine ring, a pyrrolidine ring, and an imidazoline ring.
  • Specific examples of the fused ring include naphthalene ring, anthracene ring, phenanthren ring, pyran ring, tetracene ring, indole ring, isoindole ring, benzimidazole ring, benzotriazole ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, and cinnoline. You can raise the ring.
  • the heterocyclic condensed carbazole-9-yl group is a benzofuran condensed carbazole-9-yl group, a benzothiophene condensed carbazole-9-yl group, an indole condensed carbazole-9-yl group, or a silinden condensation. It is a carbazole-9-yl group.
  • the heterocyclic condensed carbazole-9-yl group is a benzofuran condensed carbazole-9-yl group, a benzothiophene condensed carbazole-9-yl group, or an indole condensed carbazole-9-yl group. ..
  • a substituted or unsubstituted benzofuran [2,3-a] carbazole-9-yl group can be adopted as the benzofuran condensed carbazole-9-yl group.
  • a substituted or unsubstituted benzoflo [3,2-a] carbazole-9-yl group can also be adopted.
  • a substituted or unsubstituted benzoflo [2,3-b] carbazole-9-yl group can also be adopted.
  • a substituted or unsubstituted benzoflo [3,2-b] carbazole-9-yl group can also be adopted.
  • a substituted or unsubstituted benzoflo [2,3-c] carbazole-9-yl group can also be adopted.
  • a substituted or unsubstituted benzoflo [3,2-c] carbazole-9-yl group can also be adopted.
  • the preferred benzofuran-condensed carbazole-9-yl group is a carbazole-9-yl group in which only one benzofuran ring is condensed at the 2nd and 3rd positions and the other heterocycle is not condensed (the benzene ring is condensed). May be good).
  • it is a group having any of the following structures, and hydrogen atoms in the following structures may be substituted.
  • a hydrogen atom in the following structure in which a part of the hydrogen atom is substituted with a heavy hydrogen atom, or a hydrogen atom in the following structure in which all the hydrogen atoms are substituted with a heavy hydrogen atom can be preferably exemplified. Those that are not substituted can also be preferably adopted.
  • a carbazole-9-yl group in which two benzofuran rings are condensed at the 2nd and 3rd positions and the heterocycle is not condensed is also preferable (the benzene ring may be condensed).
  • the benzene ring may be condensed.
  • it is a group having any of the following structures, and hydrogen atoms in the following structures may be substituted.
  • a hydrogen atom in the following structure in which a part of the hydrogen atom is substituted with a heavy hydrogen atom or a hydrogen atom in the following structure in which all the hydrogen atoms are substituted with a heavy hydrogen atom can be preferably exemplified. Those that are not substituted can also be preferably adopted.
  • a substituted or unsubstituted benzothioeno [2,3-a] carbazole-9-yl group can be adopted as the benzothiophene condensed carbazole-9-yl group. Further, a substituted or unsubstituted benzothieno [3,2-a] carbazole-9-yl group can also be adopted. Further, a substituted or unsubstituted benzothieno [2,3-b] carbazole-9-yl group can also be adopted. Further, a substituted or unsubstituted benzothieno [3,2-b] carbazole-9-yl group can also be adopted.
  • a substituted or unsubstituted benzothieno [2,3-c] carbazole-9-yl group can also be adopted.
  • a substituted or unsubstituted benzothieno [3,2-c] carbazole-9-yl group can also be adopted.
  • a preferred benzothiophene-fused carbazole-9-yl group is a carbazole-9-yl group in which only one benzothiophene ring is condensed at the 2nd and 3rd positions and the other heterocycle is not condensed (the benzene ring is condensed). May be). Specifically, it is a group having any of the following structures, and hydrogen atoms in the following structures may be substituted.
  • a hydrogen atom in the following structure in which a part of the hydrogen atom is substituted with a heavy hydrogen atom, or a hydrogen atom in the following structure in which all the hydrogen atoms are substituted with a heavy hydrogen atom can be preferably exemplified. Those that are not substituted can also be preferably adopted.
  • a carbazole-9-yl group in which two benzothiophene rings are condensed at the 2nd and 3rd positions and the heterocycle is not condensed is also preferable (the benzene ring may be condensed).
  • the benzene ring may be condensed.
  • it is a group having any of the following structures, and hydrogen atoms in the following structures may be substituted.
  • a hydrogen atom in the following structure in which a part of the hydrogen atom is substituted with a heavy hydrogen atom, or a hydrogen atom in the following structure in which all the hydrogen atoms are substituted with a heavy hydrogen atom can be preferably exemplified. Those that are not substituted can also be preferably adopted.
  • a substituted or unsubstituted indro [2,3-a] carbazole-9-yl group can be adopted as the indole condensed carbazole-9-yl group. Further, a substituted or unsubstituted indro [3,2-a] carbazole-9-yl group can also be adopted. Further, a substituted or unsubstituted indro [2,3-b] carbazole-9-yl group can also be adopted. Further, a substituted or unsubstituted indro [3,2-b] carbazole-9-yl group can also be adopted. Further, a substituted or unsubstituted indro [2,3-c] carbazole-9-yl group can also be adopted.
  • a substituted or unsubstituted indro [3,2-c] carbazole-9-yl group can also be adopted.
  • the preferred indole-condensed carbazole-9-yl group is a carbazole-9-yl group in which only one indole ring is condensed at the 2nd and 3rd positions and the other heterocycle is not condensed (the benzene ring is condensed). May be good).
  • R'in the following structure represents a hydrogen atom, a deuterium atom or a substituent (preferably R'is a substituent).
  • R' is preferably a substituted or unsubstituted aryl group.
  • the hydrogen atom in the following structure may be substituted.
  • a hydrogen atom in the following structure in which a part of the hydrogen atom is substituted with a heavy hydrogen atom, or a hydrogen atom in the following structure in which all the hydrogen atoms are substituted with a heavy hydrogen atom can be preferably exemplified. Those that are not substituted can also be preferably adopted.
  • the heterocycle and the carbazole ring constituting the heterocyclic condensed carbazole-9-yl group may be substituted, respectively. When substituted, it may be substituted with a deuterium atom or it may be substituted with another substituent.
  • substituent here include an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group and a cyano group. can. These substituents may be substituted with yet another substituent.
  • an embodiment substituted with a heavy hydrogen atom, an alkyl group, an aryl group, an alkoxy group, and an alkylthio group can be mentioned.
  • the "alkyl group” referred to here may be linear, branched or cyclic. Further, two or more of the linear portion, the annular portion and the branched portion may be mixed.
  • the number of carbon atoms of the alkyl group can be, for example, 1 or more, 2 or more, and 4 or more. Further, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, and 4 or less.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group and isohexyl group.
  • 2-Ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group can be mentioned.
  • the alkyl group as a substituent may be further substituted with a heavy hydrogen atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom.
  • the "alkenyl group” may be linear, branched or cyclic.
  • the number of carbon atoms of the alkenyl group can be, for example, 2 or more and 4 or more. Further, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, and 4 or less.
  • Specific examples of the alkenyl group include ethenyl group, n-propenyl group, isopropenyl group, n-butenyl group, isobutenyl group, n-pentenyl group, isopentenyl group, n-hexenyl group, isohexenyl group and 2-ethylhexenyl group. Can be mentioned.
  • the alkenyl group as a substituent may be further substituted.
  • the "aryl group” and the “heteroaryl group” may be a monocyclic ring or a condensed ring in which two or more rings are condensed. In the case of fused rings, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4.
  • the ring include a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a quinoline ring, a pyrazine ring, a quinoxaline ring, and a naphthylidine ring.
  • arylene group or the heteroarylene group examples include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthrasenyl group, a 2-anthrasenyl group, a 9-anthrasenyl group, a 2-pyridyl group, a 3-pyridyl group, and 4 -Pyridyl groups can be mentioned.
  • the alkyl moiety of the "alkoxy group” and the "alkylthio group the above description and specific examples of the alkyl group can be referred to.
  • the heterocyclic condensed carbazole-9-yl group preferably has 16 or more atoms other than hydrogen atoms and deuterium atoms, more preferably 20 or more, and may be, for example, 16 or more. Further, it is preferably 80 or less, more preferably 50 or less, and further preferably 30 or less.
  • the heterocyclic condensed carbazole-9-yl group may be only D 1 or only D 2 .
  • both D 1 and D 2 are heterocyclic condensed carbazole-9-yl groups.
  • D 1 and D 2 may have the same structure or may have different heterocyclic condensed carbazole-9-yl groups.
  • the other is a donor group other than the heterocyclic condensed carbazole-9-yl group (hereinafter referred to as "another donor group").
  • another donor group is a donor group having a negative Hammet's ⁇ p value.
  • k is the rate constant of the benzene derivative having no substituent
  • k 0 is the rate constant of the benzene derivative substituted with the substituent
  • K is the equilibrium constant of the benzene derivative having no substituent
  • K 0 is the substituent.
  • the equilibrium constant of the benzene derivative substituted with, ⁇ represents the reaction constant determined by the type and conditions of the reaction.
  • ⁇ p value refers to the description of ⁇ p value in Hansch, C.et.al., Chem.Rev., 91,165-195 (1991). can. Groups with a negative Hammett ⁇ p value tend to show electron donating properties (donor properties), and groups with positive Hammett ⁇ p values tend to show electron attractor properties (acceptor properties).
  • the other donor group in the present invention is preferably a group containing a substituted amino group.
  • the substituent bonded to the nitrogen atom of the amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group is more preferable.
  • the substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group.
  • the donor group in the present invention may be a group bonded with a nitrogen atom of a substituted amino group or a group bonded with a group to which a substituted amino group is bonded.
  • the group to which the substituted amino group is bonded is preferably a ⁇ -conjugated group. More preferred are groups bonded at the nitrogen atom of the substituted amino group.
  • the alkyl group, alkenyl group, aryl group and heteroaryl group which are the substituents here the above-mentioned corresponding description regarding the substituent of the aromatic hydrocarbon ring group and the aromatic heterocyclic group can be referred to.
  • Particularly preferred as the other donor group in the present invention is a substituted or unsubstituted carbazole-9-yl group.
  • the carbazole-9-yl group may be further condensed with a benzene ring or a heterocycle (excluding the benzofuran ring, the benzothiophene ring, the indole ring, the indene ring, and the sirainden ring).
  • the substituent of the carbazole-9-yl group includes an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group and a substituted amino.
  • a group can be mentioned, and preferred substituents include an alkyl group, an aryl group, and a substituted amino group.
  • the substituted amino group referred to here includes a substituted or unsubstituted carbazolyl group, for example, a substituted or unsubstituted carbazole-3-yl group and a substituted or unsubstituted carbazole-9-yl group.
  • the other donor group in the present invention preferably has 8 or more atoms other than hydrogen atoms and deuterium atoms, more preferably 12 or more, and may be, for example, 16 or more. Further, it is preferably 80 or less, more preferably 60 or less, and further preferably 40 or less.
  • D13 to D78, D84 to D119, D150 to D161, D168 to D209, D215 to D268, D270 to D324 are specific examples of the heterocyclic condensed carbazole-9-yl group, and D1 to D12, D79 to 83, D120 to 149.
  • D162-D167, D210-D214, D269 are specific examples of other donor groups.
  • Ph represents a phenyl group and * represents a bond position.
  • R in the general formula (1) is a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded with a carbon atom.
  • R is a hydrogen atom or a deuterium atom.
  • R is a substituted or unsubstituted aryl group or an embodiment in which R is a substituted or unsubstituted heteroaryl group bonded at a carbon atom.
  • R is an aryl group, it is preferably a substituted aryl group.
  • R is a heteroaryl group, it is preferably a substituted heteroaryl group.
  • Ar in the general formula (1) is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded at a carbon atom.
  • Ar is a substituted or unsubstituted aryl group.
  • an embodiment in which Ar is a substituted or unsubstituted heteroaryl group can also be adopted.
  • the description and preferable range of the aryl group and the heteroaryl group that can be taken by R and Ar the description of the aryl group and the heteroaryl group in the substituent of the heterocyclic condensed carbazole-9-yl group can be referred to.
  • the heteroaryl group is a heteroaryl group bonded at a carbon atom.
  • Aryl group substituents and heteroaryl group substituents include alkyl groups, alkenyl groups, aryl groups, heteroaryl groups, alkoxy groups, alkylthio groups, aryloxy groups, arylthio groups, heteroaryloxy groups, and heteroarylthio groups.
  • Cyano groups can be mentioned. These substituents may be substituted with yet another substituent.
  • Preferred groups of substituents include an alkyl group, an aryl group, an alkoxy group, an alkylthio group and a cyano group.
  • R is a hydrogen atom or a deuterium atom and Ar is a substituted or unsubstituted phenyl group (the phenyl group is selected from a benzene ring, a pyridine ring, a furan ring, a thiophene ring and a pyrrole ring. One or more rings may be condensed).
  • R is a hydrogen atom or a deuterium atom and Ar is a substituted or unsubstituted pyridyl group (the pyridyl group is composed of a benzene ring, a pyridine ring, a furan ring, a thiophene ring and a pyrrole ring. One or more rings selected may be fused).
  • R is a hydrogen atom or a deuterium atom and Ar is a substituted phenyl group (the phenyl group is selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted pyridyl group.
  • R is a hydrogen atom or a deuterium atom and Ar is a substituted pyridyl group (the pyridyl group is selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted pyridyl group.
  • One or more groups are substituted).
  • the compound represented by the general formula (1) may be a compound composed of only an atom selected from the group consisting of a carbon atom, a hydrogen atom, a heavy hydrogen atom, a nitrogen atom, an oxygen atom and a sulfur atom.
  • the compound represented by the general formula (1) is composed only of an atom selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom and an oxygen atom.
  • the compound represented by the general formula (1) may be a compound composed of only an atom selected from the group consisting of a carbon atom, a hydrogen atom, a heavy hydrogen atom, a nitrogen atom and a sulfur atom.
  • the compound represented by the general formula (1) may be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms and nitrogen atoms. Further, the compound represented by the general formula (1) may be a compound containing a deuterium atom without containing a hydrogen atom. For example, the compound represented by the general formula (1) may be a compound composed of only an atom selected from the group consisting of a carbon atom, a heavy hydrogen atom, a nitrogen atom, an oxygen atom and a sulfur atom. In one aspect of the present invention, the compound represented by the general formula (1) has a symmetrical structure.
  • the compound represented by the general formula (1) has a structure represented by the following general formula (2).
  • the compound represented by the general formula (1) has a structure represented by the following general formula (3).
  • R 1 to R 4 of the following general formula for each compound corresponds to R 1 of the following general formula
  • D 1 of the general formula (1) corresponds to R 2 of the following general formula. If a rotational isomer is present among the following compounds, the mixture of the rotational isomer and each separated rotational isomer are also disclosed in the present specification.
  • the compounds in which H of R 1 is substituted with D in the compounds 1 to 6300 are disclosed here as compounds 6301 to 12600 in order.
  • Compounds 1 to 6300 in which R 1 and R 4 are exchanged to form R 4 and R 1 are disclosed herein as compounds 12601 to 18900.
  • the compounds in which H of R 2 is substituted with D in the compounds 12601 to 18900 are disclosed here as compounds 18901 to 25200 in order.
  • Compounds 1 to 6300 in which R 1 , R 2 , R 3 , and R 4 are designated as R 3 , R 1 , R 4 , and R 2 in that order are disclosed here as compounds 25201 to 31500.
  • the compounds of the H of R 3 was replaced to D in compounds 25201-31500, disclosed herein as compounds 31501-37800 sequentially.
  • the compounds in which R 1 , R 2 , R 3 , and R 4 in compounds 1 to 6300 are designated as R 4 , R 1 , R 2 , and R 3 in this order are disclosed here as compounds 37801 to 44100.
  • Compounds 1 to 6300 in which R 1 , R 3 , and R 4 are replaced to form R 3 , R 4 , and R 1 are disclosed here as compounds 50401 to 56700.
  • the compounds of the H of R 3 was replaced to D in compounds 50401-56700, disclosed herein as compounds 56701-63000 sequentially.
  • Compounds 1 to 6300 in which R 3 and R 4 are replaced to form R 4 and R 3 are disclosed herein as compounds 63001 to 69300.
  • the compounds in which H of R 1 is substituted with D in the compounds 63001 to 69300 are disclosed herein as compounds 69301 to 75600 in order.
  • Each structure of the above compounds 901 to 75600 is individually specified, and each is described as a specific compound in the present specification.
  • the molecular weight of the compound represented by the general formula (1) is, for example, 1500 or less when the organic layer containing the compound represented by the general formula (1) is intended to be formed into a film by a vapor deposition method. It is preferably 1200 or less, more preferably 1000 or less, and even more preferably 900 or less.
  • the lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1). It is preferably 624 or more.
  • the compound represented by the general formula (1) may be formed into a film by a coating method regardless of the molecular weight. By using the coating method, it is possible to form a film even if the compound has a relatively large molecular weight.
  • the compound represented by the general formula (1) has an advantage that it is easily dissolved in an organic solvent among the cyanobenzene compounds. Therefore, the compound represented by the general formula (1) is easy to apply the coating method and is easy to purify to increase the purity.
  • a compound containing a plurality of structures represented by the general formula (1) in the molecule as a light emitting material.
  • a polymer obtained by pre-existing a polymerizable group in the structure represented by the general formula (1) and polymerizing the polymerizable group as a light emitting material.
  • a monomer containing a polymerizable functional group is prepared in any of Ar, D 1 , and D 2 of the general formula (1), and this is polymerized alone or copolymerized with another monomer. Therefore, it is conceivable to obtain a polymer having a repeating unit and use the polymer as a light emitting material.
  • dimers and trimers by coupling compounds having a structure represented by the general formula (1) to each other and use them as a light emitting material.
  • a polymer having a repeating unit containing a structure represented by the general formula (1) a polymer containing a structure represented by the following general formula (4) or (5) can be mentioned.
  • Q represents a group containing the structure represented by the general formula (1)
  • L 1 and L 2 represent a linking group.
  • the carbon number of the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10.
  • X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
  • L 11 represents a linking group, preferably a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted alkylene group. It is more preferably a phenylene group.
  • R 101 , R 102 , R 103 and R 104 each independently represent a substituent.
  • the linking group represented by L 1 and L 2 can be bonded to any of Ar, D 1 , and D 2 of the general formula (1) constituting Q. Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.
  • a hydroxy group is introduced into any of Ar, D 1 and D 2 of the general formula (1), and the polymer is used as a linker as described below. It can be synthesized by reacting a compound to introduce a polymerizable group and polymerizing the polymerizable group.
  • the polymer containing the structure represented by the general formula (1) in the molecule may be a polymer consisting only of repeating units having the structure represented by the general formula (1), or may have other structures. It may be a polymer containing a repeating unit having. Further, the repeating unit having the structure represented by the general formula (1) contained in the polymer may be a single type or two or more types. Examples of the repeating unit having no structure represented by the general formula (1) include those derived from a monomer used for ordinary copolymerization. For example, a repeating unit derived from a monomer having an ethylenically unsaturated bond such as ethylene and styrene can be mentioned.
  • the compound represented by the general formula (1) is a light emitting material. In certain embodiments, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence. In one embodiment of the present disclosure, the compound represented by the general formula (1) is in the UV region, the blue, green, yellow, orange, red region of the visible spectrum when excited by thermal or electronic means. It can emit light (eg, about 420 nm to about 500 nm, about 500 nm to about 600 nm or about 600 nm to about 700 nm) or in the near infrared region.
  • the compound of the general formula (1) when excited by thermal or electronic means, is in the red or orange region of the visible spectrum (eg, from about 620 nm to about 780 nm, about 780 nm). It can emit light at 650 nm). In certain embodiments of the present disclosure, the compound of the general formula (1), when excited by thermal or electronic means, has an orange or yellow region of the visible spectrum (eg, from about 570 nm to about 620 nm, about 620 nm). It can emit light at 590 nm (about 570 nm).
  • the compound of the general formula (1) when excited by thermal or electronic means, is in the green region of the visible spectrum (eg, from about 490 nm to about 575 nm, about 510 nm). Can emit light. In certain embodiments of the present disclosure, the compound of the general formula (1), when excited by thermal or electronic means, is in the blue region of the visible spectrum (eg, from about 400 nm to about 490 nm, about 475 nm). Can emit light. In certain embodiments of the present disclosure, the compound represented by the general formula (1) can emit light in the ultraviolet spectral region (eg, 280-400 nm) when excited by thermal or electronic means. In one embodiment of the present disclosure, the compound represented by the general formula (1) can emit light in the infrared spectral region (eg, 780 nm to 2 ⁇ m) when excited by thermal or electronic means.
  • the ultraviolet spectral region eg, 280-400 nm
  • the electronic properties of small molecule chemical libraries can be calculated using known ab initio quantum chemistry calculations.
  • TD-DFT / B3LYP / 6-31G * can be analyzed and screened for molecular fragments (partial) having HOMO above a specific threshold and LUMO below a specific threshold.
  • HOMO energy for example, ionization potential
  • the receptor moiety (“A”) when there is LUMO energy (for example, electron affinity) of ⁇ 0.5 eV or less, the receptor moiety (“A”) can be selected.
  • the bridge moiety (“B”) is, for example, a strong conjugated system that can severely limit the acceptor and donor moieties to specific conformations, resulting in overlap between the ⁇ -conjugated system of the donor and acceptor moieties.
  • compound libraries are sorted using one or more of the following properties: 1. 1. Emission near a specific wavelength 2. Calculated triplet state above a specific energy level 3. Delta] E ST value 4 below a certain value. Quantum yield above a specific value 5. HOMO level 6.
  • the difference between the lowest triplet excited state of the singlet excited state and the lowest in the 77K ( ⁇ E ST) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, Less than about 0.2 eV or less than about 0.1 eV.
  • E ST value some embodiments, less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03eV , Less than about 0.02 eV or less than about 0.01 eV.
  • the compound represented by the general formula (1) is in excess of 25%, eg, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%. , About 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or higher quantum yields.
  • the compound represented by the general formula (1) is a novel compound.
  • the compound represented by the general formula (1) can be synthesized by combining known reactions. For example, be synthesized by reaction in tetrahydrofuran in the presence of sodium hydride to D 1 -H and D 2 -H in difluoro isophthalonitrile position has been substituted with fluorine atoms to be introduced D 1, D 2 Is possible. When D 1 and D 2 are different from each other , the reaction with D 1- H and D 2- H may be carried out in two steps. For specific reaction conditions and reaction procedures, a synthetic example described later can be referred to.
  • the compound represented by the general formula (1) it is combined with a compound represented by the general formula (1), the compound is dispersed, covalently bonded to the compound, coated with the compound, carried or associated with the compound 1. Used with one or more materials (eg, small molecules, polymers, metals, metal complexes, etc.) to form solid films or layers.
  • the compound represented by the general formula (1) can be combined with an electrically active material to form a film.
  • the compound represented by the general formula (1) may be combined with the hole transport polymer.
  • the compound represented by the general formula (1) may be combined with the electron transport polymer.
  • the compound represented by the general formula (1) may be combined with the hole transport polymer and the electron transport polymer. In some cases, the compound represented by the general formula (1) may be combined with a copolymer having both a hole transport part and an electron transport part. According to the above embodiment, the electrons and / or holes formed in the solid film or layer can interact with the compound represented by the general formula (1).
  • the film containing the compound of the present invention represented by the general formula (1) can be formed by a wet step.
  • a solution in which the composition containing the compound of the present invention is dissolved is applied to the surface, and a film is formed after removing the solvent.
  • the wet process include, but are not limited to, a spin coating method, a slit coating method, an inkjet method (spray method), a gravure printing method, an offset printing method, and a flexographic printing method.
  • an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used.
  • a substituent eg, an alkyl group
  • the film containing the compound of the invention can be formed in a dry process.
  • the vacuum deposition method can be employed as the dry process, without limitation. When the vacuum vapor deposition method is adopted, the compounds constituting the film may be co-deposited from individual vapor deposition sources, or may be co-deposited from a single vapor deposition source in which the compounds are mixed.
  • a mixed powder in which a powder of the compound is mixed may be used, a compression molded product obtained by compressing the mixed powder may be used, or each compound is heated and melted and cooled.
  • a mixture may be used.
  • the composition ratio of the plurality of compounds contained in the vapor deposition source is obtained by performing co-evaporation under the condition that the vapor deposition rates (weight reduction rates) of the plurality of compounds contained in a single vapor deposition source are the same or almost the same. It is possible to form a film having a composition ratio corresponding to the above.
  • a film having a desired composition ratio can be easily formed.
  • a temperature at which each compound to be co-deposited has the same weight loss rate can be specified, and that temperature can be adopted as the temperature at the time of co-depositing.
  • Organic light emitting diode One aspect of the present invention relates to the use of a compound represented by the general formula (1) of the present invention as a light emitting material for an organic light emitting device.
  • the compound represented by the general formula (1) of the present invention can be effectively used as a light emitting material in the light emitting layer of the organic light emitting element.
  • the compound represented by the general formula (1) comprises delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence.
  • the present invention provides a delayed fluorophore having a structure represented by the general formula (1).
  • the present invention relates to the use of a compound represented by the general formula (1) as a delayed fluorophore.
  • the compound of the present invention is represented by the general formula (1), which can be used as a host material and can be used with one or more light emitting materials, wherein the light emitting material is a fluorescent material. It may be a phosphorescent material or TADF.
  • the compound represented by the general formula (1) can also be used as a hole transport material.
  • the compound represented by the general formula (1) can be used as an electron transporting material.
  • the present invention relates to a method of causing delayed fluorescence from a compound represented by the general formula (1).
  • the organic light emitting element containing the compound as a light emitting material emits delayed fluorescence and exhibits high light emission efficiency.
  • the light emitting layer comprises a compound represented by the general formula (1), the compound represented by the general formula (1) being oriented parallel to the substrate.
  • the substrate is a film-forming surface.
  • the orientation of the compound represented by the general formula (1) with respect to the film-forming surface affects or determines the direction of propagation of the light emitted by the compound to be aligned.
  • the efficiency of light extraction from the light emitting layer is improved by aligning the propagation directions of the light emitted by the compound represented by the general formula (1).
  • the organic light emitting device comprises a light emitting layer.
  • the light emitting layer comprises a compound represented by the general formula (1) as a light emitting material.
  • the organic light emitting device is an organic light luminescence device (organic PL element).
  • the organic light emitting device is an organic electroluminescence device (organic EL device).
  • the compound represented by the general formula (1) assists the light emission of other light emitting materials contained in the light emitting layer (as a so-called assist dopant).
  • the compound represented by the general formula (1) contained in the light emitting layer is at its lowest excited singlet energy level and with the lowest excited singlet energy level of the host material contained in the light emitting layer. It is included between the lowest excited singlet energy levels of other light emitting materials contained in the light emitting layer.
  • the organic light luminescence device comprises at least one light emitting layer.
  • the organic electroluminescence device comprises at least an anode, a cathode, and an organic layer between the anode and the cathode.
  • the organic layer comprises at least a light emitting layer.
  • the organic layer comprises only a light emitting layer.
  • the organic layer comprises one or more organic layers in addition to the light emitting layer.
  • the organic layer include a hole transport layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transport layer and an exciton barrier layer.
  • the hole transport layer may be a hole injection transport layer having a hole injection function
  • the electron transport layer may be an electron injection transport layer having an electron injection function.
  • the light emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons.
  • the layer emits light.
  • only the light emitting material is used as the light emitting layer.
  • the light emitting layer comprises a light emitting material and a host material.
  • the light emitting material is one or more compounds of the general formula (1).
  • the single term exciter and the triple term exciter generated in the light emitting material are confined in the light emitting material.
  • a host material is used in addition to the light emitting material in the light emitting layer.
  • the host material is an organic compound.
  • the organic compound has an excited singlet energy and an excited triplet energy, at least one of which is higher than those of the light emitting materials of the present invention.
  • the singlet and triplet excitons generated in the luminescent material of the invention are confined in the molecule of the luminescent material of the invention. In certain embodiments, singlet and triplet excitons are sufficiently confined to improve photoradiation efficiency.
  • singlet and triplet excitons are not sufficiently confined, even though high photoradiation efficiency is still obtained, i.e., host materials capable of achieving high photoradiation efficiency are particularly limited. Can be used in the present invention without any need.
  • light emission occurs in the light emitting material in the light emitting layer of the device of the present invention.
  • the emitted light comprises both fluorescence and delayed fluorescence.
  • the radiated light includes radiated light from the host material.
  • the radiated light consists of synchrotron radiation from the host material.
  • the synchrotron radiation includes synchrotron radiation from a compound represented by the general formula (1) and synchrotron radiation from a host material.
  • TADF molecules and host materials are used.
  • TADF is an assist dopant.
  • various compounds can be adopted as a light emitting material (preferably a fluorescent material).
  • luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stylben derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, and terphenyl derivatives.
  • Turphenylene derivatives fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, durolysin derivatives, thiazole derivatives, derivatives having metals (Al, Zn), etc. can be used. be.
  • These exemplary skeletons may or may not have substituents. Further, these exemplary skeletons may be combined with each other.
  • a light emitting material that can be used in combination with the assist dopant represented by the general formula (1) will be illustrated.
  • the compound described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be particularly preferably adopted as a light emitting material used together with the assist dopant represented by the general formula (1).
  • the amount of the compound of the present invention as the light emitting material contained in the light emitting layer is 0.1% by weight or more. In certain embodiments, when the host material is used, the amount of the compound of the present invention as the light emitting material contained in the light emitting layer is 1% by weight or more. In certain embodiments, when the host material is used, the amount of the compound of the present invention as the light emitting material contained in the light emitting layer is 50% by weight or less. In certain embodiments, when the host material is used, the amount of the compound of the present invention as the light emitting material contained in the light emitting layer is 20% by weight or less.
  • the amount of the compound of the present invention as the light emitting material contained in the light emitting layer is 10% by weight or less.
  • the host material of the light emitting layer is an organic compound having a hole transport function and an electron transport function.
  • the host material for the light emitting layer is an organic compound that prevents the wavelength of the synchrotron radiation from increasing.
  • the host material for the light emitting layer is an organic compound with a high glass transition temperature.
  • the host material is selected from the group consisting of:
  • the light emitting layer comprises two or more differently structured TADF molecules. For example, a light emitting layer containing these three materials in which the excited singlet energy level is higher in the order of the host material, the first TADF molecule, and the second TADF molecule can be obtained.
  • the 1TADF molecule with a 2TADF molecule is preferably both a difference Delta] E ST of the lowest excited triplet energy level of the lowest excited singlet energy level and 77K or less 0.3 eV, below 0.25eV It is more preferably 0.2 eV or less, more preferably 0.15 eV or less, further preferably 0.1 eV or less, still more preferably 0.07 eV or less. , 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less.
  • the content of the first TADF molecule in the light emitting layer is preferably higher than the content of the second TADF molecule.
  • the content of the host material in the light emitting layer is preferably higher than the content of the second TADF molecule.
  • the content of the first TADF molecule in the light emitting layer may be higher, lower, or the same as the content of the host material.
  • the composition in the light emitting layer may be 10 to 70% by weight of the host material, 10 to 80% by weight of the first TADF molecule, and 0.1 to 30% by weight of the second TADF molecule.
  • the composition in the light emitting layer may be 20 to 45% by weight of the host material, 50 to 75% by weight of the first TADF molecule, and 5 to 20% by weight of the second TADF molecule.
  • the emission quantum yield ⁇ PL2 (A) due to photoexcitation of the co-deposited film of the material satisfies the relational expression of ⁇ PL1 (A)> ⁇ PL2 (A).
  • the emission quantum yield ⁇ PL2 (B) by photoexcitation of the co-deposited film of the second TADF molecule and the host material (content of the second TADF molecule in this co-deposited film B wt%) and the second TADF molecule alone.
  • the emission quantum yield ⁇ PL2 (100) due to photoexcitation of the film satisfies the relational expression of ⁇ PL2 (B)> ⁇ PL2 (100).
  • the light emitting layer can contain three structurally different TADF molecules.
  • the compound of the present invention may be any of a plurality of TADF compounds contained in the light emitting layer.
  • the light emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light emitting material. In certain embodiments, the light emitting layer is free of metallic elements. In certain embodiments, the light emitting layer can be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, dehydrogen atoms, nitrogen atoms, oxygen atoms and sulfur atoms. Alternatively, the light emitting layer may be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms.
  • the light emitting layer may be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms.
  • the TADF material may be a known delayed fluorescent material.
  • Preferred delayed fluorescent materials include paragraphs 0008 to 0048 and 0995 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 985 of WO2013 / 011954, and paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 01955.
  • those capable of emitting delayed fluorescence can be preferably adopted.
  • the above publications described in this paragraph are hereby incorporated herein by reference.
  • the organic electroluminescence device of the present invention is held by a substrate, the substrate is not particularly limited and is commonly used in organic electroluminescence devices, such as glass, clear plastic, quartz and silicon. Any material formed by the above may be used.
  • the anode of an organic electroluminescence device is manufactured from a metal, alloy, conductive compound or a combination thereof.
  • the metal, alloy or conductive compound has a high work function (4 eV or higher).
  • the metal is Au.
  • the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO 2 and ZnO.
  • an amorphous material capable of forming a transparent conductive film such as IDIXO (In 2 O 3-ZnO), is used.
  • the anode is a thin film. In some embodiments, the thin film is made by vapor deposition or sputtering.
  • the film is patterned by a photolithography method.
  • the pattern may be formed using a mask having a shape suitable for vapor deposition or sputtering on the electrode material.
  • a wet film forming method such as a printing method or a coating method is used.
  • synchrotron radiation passes through the anode, the anode has a transmittance of more than 10% and the anode has a sheet resistance of no more than a few hundred ohms per unit area.
  • the thickness of the anode is 10-1,000 nm. In some embodiments, the thickness of the anode is 10-200 nm. In some embodiments, the thickness of the anode will vary depending on the material used.
  • the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injected metal), an alloy, a conductive compound or a combination thereof.
  • the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al 2). O 3 ) Selected from mixtures, indium, lithium-aluminum mixtures and rare earth elements.
  • a mixture of the electron-injected metal and a second metal which is a stable metal with a higher work function than the electron-injected metal, is used.
  • the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al 2 O 3 ) mixture, a lithium-aluminum mixture and aluminum.
  • the mixture improves electron injection properties and resistance to oxidation.
  • the cathode is manufactured by forming the electrode material as a thin film by vapor deposition or sputtering.
  • the cathode has a sheet resistance of tens of ohms or less per unit area.
  • the cathode has a thickness of 10 nm to 5 ⁇ m.
  • the thickness of the cathode is 50-200 nm.
  • any one of the anode and cathode of the organic electroluminescence element is transparent or translucent in order to transmit synchrotron radiation.
  • the transparent or translucent electroluminescent device improves the light radiance.
  • the cathode is formed of the conductive transparent material described above with respect to the anode to form a transparent or translucent cathode.
  • the device comprises an anode and a cathode, both of which are transparent or translucent.
  • the injection layer is the layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the drive voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be arranged between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, there is no injection layer. The following are examples of preferable compounds that can be used as hole injection materials.
  • the barrier layer is a layer capable of preventing charges (electrons or holes) and / or excitons present in the light emitting layer from diffusing outside the light emitting layer.
  • the electron barrier layer resides between the light emitting layer and the hole transport layer, preventing electrons from passing through the light emitting layer to the hole transport layer.
  • the hole barrier layer exists between the light emitting layer and the electron transport layer to prevent holes from passing through the light emitting layer to the electron transport layer.
  • the barrier layer prevents excitons from diffusing outside the light emitting layer.
  • the electron barrier layer and the hole barrier layer constitute an exciton barrier layer.
  • the term "electron barrier layer" or "exciton barrier layer” includes both an electron barrier layer and a layer having both the functions of an exciton barrier layer.
  • Hole barrier layer functions as an electron transport layer. In some embodiments, the hole barrier layer prevents holes from reaching the electron transport layer during electron transport. In some embodiments, the hole barrier layer increases the probability of electron-hole recombination in the light emitting layer.
  • the material used for the hole barrier layer may be the same material as described above for the electron transport layer. The following are examples of preferable compounds that can be used for the hole barrier layer.
  • the electron barrier layer transports holes.
  • the electron barrier layer blocks electrons from reaching the hole transport layer during hole transport.
  • the electron barrier layer increases the probability of electron-hole recombination in the light emitting layer.
  • the material used for the electron barrier layer may be the same material as described above for the hole transport layer. Specific examples of preferable compounds that can be used as an electron barrier material are given below.
  • Exciton barrier layer prevents excitons generated through recombination of holes and electrons in the light emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton barrier layer allows for effective exciton confinement in the light emitting layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton barrier layer is adjacent to the light emitting layers on either the anode side and the cathode side, and on either side of the anode side. In some embodiments, when the exciton barrier layer is present on the anode side, the layer may be present between the hole transport layer and the light emitting layer and adjacent to the light emitting layer.
  • the layer when the exciton barrier layer is present on the cathode side, the layer may be present between the light emitting layer and the cathode and adjacent to the light emitting layer.
  • a hole injection layer, an electron barrier layer or a similar layer resides between the anode and the exciton barrier layer adjacent to the light emitting layer on the anode side.
  • the hole injection layer, electron barrier layer, hole barrier layer or similar layer is present between the cathode and the exciton barrier layer adjacent to the light emitting layer on the cathode side.
  • the excited element barrier layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and the excited triplet energy of the light emitting material, respectively.
  • the hole transport layer contains a hole transport material.
  • the hole transport layer is monolayer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the hole injection or transport properties and the electron barrier properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention are, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane inducers, pyrazoline derivatives, pyrazolones.
  • the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds.
  • the hole transport material is an aromatic tertiary amine compound. Specific examples of preferable compounds that can be used as hole transport materials are given below.
  • Electron transport layer contains an electron transport material.
  • the electron transport layer is monolayer.
  • the electron transport layer has multiple layers.
  • the electron transport material only needs to have the function of transporting the electrons injected from the cathode to the light emitting layer.
  • the electron transport material also functions as a hole barrier material.
  • electron transport layers examples include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthracinodimethanes, anthrone derivatives, and oxadi. Examples thereof include azole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof.
  • the electron transport material is a thiadiazole inducer or a quinoxaline derivative.
  • the electron transport material is a polymeric material. Specific examples of preferable compounds that can be used as electron transport materials are given below.
  • preferable compounds as materials that can be added to each organic layer are given.
  • it may be added as a stabilizing material.
  • the light emitting layer is incorporated into the device.
  • devices include, but are not limited to, OLED valves, OLED lamps, television displays, computer monitors, mobile phones and tablets.
  • the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising a light emitting layer between the anode and the cathode.
  • the components described herein can be incorporated into a variety of photosensitive or photoactivating devices, such as OLEDs or optoelectronic devices.
  • the construct may be useful for facilitating charge transfer or energy transfer within the device and / or as a hole transport material.
  • Examples of the device include an organic light emitting diode (OLED), an organic integrated line (OIC), an organic field effect transistor (O-FET), an organic thin film (O-TFT), an organic light emitting transistor (O-LET), and an organic solar cell. (O-SC), organic optical detectors, organic photoreceivers, organic field-quench devices (O-FQD), light emitting fuel cells (LECs) or organic laser diodes (O-lasers).
  • OLED organic light emitting diode
  • OIC organic integrated line
  • O-FET organic field effect transistor
  • OFTFT organic thin film
  • O-LET organic light emitting transistor
  • O-SC organic solar cell.
  • O-SC organic solar cell.
  • organic optical detectors organic photoreceivers
  • O-FQD organic field-quench devices
  • LOCs light emitting fuel cells
  • O-lasers organic laser diodes
  • the electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising a light emitting layer between the anode and the cathode.
  • the device comprises an OLED of different colors.
  • the device comprises an array containing a combination of OLEDs.
  • the combination of OLEDs is a combination of three colors (eg RGB).
  • the combination of OLEDs is a combination of colors that are neither red nor green nor blue (eg, orange and yellow-green).
  • the combination of OLEDs is a combination of two colors, four colors or more.
  • the device is A circuit board having a first surface with a mounting surface and a second surface opposite the mounting surface and defining at least one opening.
  • At least one OLED that has The housing for the circuit board and An OLED light comprising at least one connector located at the end of the housing, wherein the housing and the connector define a package suitable for mounting in lighting equipment.
  • the OLED light has a plurality of OLEDs mounted on a circuit board such that light is emitted in multiple directions.
  • some light emitted in the first direction is polarized and emitted in the second direction.
  • a reflector is used to polarize the light emitted in the first direction.
  • the light emitting layer of the present invention can be used in a screen or display.
  • the compounds according to the invention are deposited onto a substrate using steps such as, but not limited to, vacuum evaporation, deposition, vapor deposition or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in two-sided etching that provides pixels with a unique aspect ratio.
  • the screen also referred to as a mask
  • the design of the corresponding artwork pattern allows the placement of very steep, narrow tie bars between pixels in the vertical direction, as well as large, wide-ranging bevel openings in the horizontal direction.
  • the preferred material for the vapor deposition mask is Invar.
  • Invar is a metal alloy that is cold-rolled into a long thin sheet at a steel mill. Invar cannot be electrodeposited onto the spin mandrel as a nickel mask.
  • a suitable and low-cost method for forming an opening region in a vapor deposition mask is a wet chemical etching method.
  • the screen or display pattern is a pixel matrix on a substrate.
  • the screen or display pattern is processed using lithography (eg, photolithography and e-beam lithography).
  • the screen or display pattern is processed using wet chemical etching.
  • the screen or display pattern is processed using plasma etching.
  • the OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel in cell panel units. Normally, each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and a source / drain electrode on a base substrate, a flattening film is applied to the TFT, and a pixel electrode and a light emitting layer are applied. , The counter electrode and the encapsulating layer are formed in order over time, and are formed by cutting from the mother panel.
  • TFT thin film transistor
  • the OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel in cell panel units.
  • each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and a source / drain electrode on a base substrate, a flattening film is applied to the TFT, and a pixel electrode and a light emitting layer are applied.
  • TFT thin film transistor
  • the counter electrode and the encapsulating layer are formed in order over time, and are formed by cutting from the mother panel.
  • a method of manufacturing an organic light emitting diode (OLED) display is provided, wherein the method is: The process of forming a barrier layer on the base base material of the mother panel, A step of forming a plurality of display units on a cell panel unit on the barrier layer, A step of forming an encapsulation layer on each of the display units of the cell panel, A step of applying an organic film to the interface portion between the cell panels is included.
  • the barrier layer is, for example, an inorganic film formed of SiNx, the edges of the barrier layer being coated with an organic film formed of polyimide or acrylic.
  • the organic film helps the mother panel to be softly cut in cell panel units.
  • the thin film transistor (TFT) layer comprises a light emitting layer, a gate electrode, and a source / drain electrode.
  • Each of the plurality of display units may have a thin film transistor (TFT) layer, a flattening film formed on the TFT layer, and a light emitting unit formed on the flattening film, and the interface portion may have a light emitting unit.
  • the applied organic film is formed of the same material as the flattening film, and is formed at the same time as the flattening film is formed.
  • the light emitting unit is coupled to the TFT layer by a passivation layer, a flattening film in between, and an encapsulating layer that coats and protects the light emitting unit.
  • the organic film is not coupled to either the display unit or the encapsulation layer.
  • each of the organic film and the flattening film may contain any one of polyimide and acrylic.
  • the barrier layer may be an inorganic film.
  • the base substrate may be made of polyimide.
  • the method further comprises a step of attaching a carrier substrate made of a glass material to the other surface of the base substrate before forming a barrier layer on one surface of the base substrate made of polyimide. It may include a step of separating the carrier substrate from the base substrate prior to cutting along the interface portion.
  • the OLED display is a flexible display.
  • the passivation layer is an organic film placed on the TFT layer for coating the TFT layer.
  • the flattening film is an organic film formed on the passivation layer.
  • the flattening film is made of polyimide or acrylic, similar to the organic film formed at the ends of the barrier layer. In some embodiments, the flattening film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed at the edges of the barrier layer, whereby a portion of the organic film is in direct contact with the base substrate and the rest of the organic film is removed. , Surrounding the edge of the barrier layer and in contact with the barrier layer.
  • the light emitting layer has a pixel electrode, a counter electrode, and an organic light emitting layer disposed between the pixel electrode and the counter electrode.
  • the pixel electrode is connected to a source / drain electrode in the TFT layer.
  • an appropriate voltage is formed between the pixel electrode and the counter electrode so that the organic light emitting layer emits light, thereby the image. Is formed.
  • the image forming unit having the TFT layer and the light emitting unit will be referred to as a display unit.
  • the encapsulation layer that covers the display unit and prevents the penetration of external moisture may be formed in a thin film encapsulation structure in which organic films and inorganic films are alternately laminated.
  • the encapsulation layer has a thin film encapsulation structure in which a plurality of thin films are laminated.
  • the organic film applied to the interface section is spaced apart from each of the plurality of display units.
  • the organic film is formed in such a manner that some of the organic films are in direct contact with the base substrate and the rest of the organic film surrounds the edges of the barrier layer while in contact with the barrier layer. Will be done.
  • the OLED display is flexible and uses a flexible base substrate made of polyimide.
  • the base substrate is formed on a carrier substrate made of a glass material, which is then separated.
  • the barrier layer is formed on the surface of the base substrate opposite the carrier substrate.
  • the barrier layer is patterned according to the size of each cell panel. For example, a base substrate is formed on all surfaces of the mother panel, while a barrier layer is formed according to the size of each cell panel, thereby forming a groove in the interface portion between the barrier layers of the cell panel. Each cell panel can be cut along the groove.
  • the manufacturing method further comprises the step of cutting along an interface portion, where a groove is formed in the barrier layer, at least a portion of the organic film is formed in the groove, and the groove is formed. Does not penetrate the base substrate.
  • a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a flattening film, which is an organic film, are placed on the TFT layer to cover the TFT layer.
  • a polyimide or acrylic flattening film is formed, for example, the groove of the interface portion is covered with an organic film made of polyimide or acrylic, for example.
  • the groove of the interface portion between the barrier layers is covered with an organic film to absorb the impact that can be transmitted to the barrier layer without the organic film, so that each cell panel is softly cut and the barrier layer is used. It may be prevented from cracking.
  • the organic film and the flattening film covering the grooves of the interface portion are arranged at intervals from each other.
  • the organic film and the flattening film are interconnected as one layer, external moisture may infiltrate into the display unit through the flattening film and the portion where the organic film remains.
  • the organic film and the flattening film are spaced apart from each other so that the organic film is spaced apart from the display unit.
  • the display unit is formed by the formation of a light emitting unit and the encapsulation layer is placed on the display unit to cover the display unit.
  • the carrier base material that supports the base base material is separated from the base base material.
  • the carrier substrate is separated from the base substrate due to the difference in the coefficient of thermal expansion between the carrier substrate and the base substrate.
  • the mother panel is cut in cell panel units.
  • the mother panel is cut along the interface between the cell panels using a cutter.
  • the grooves in the interface section where the mother panel is cut are covered with an organic film so that the organic film absorbs the impact during cutting.
  • the barrier layer can be prevented from cracking during cutting. In some embodiments, the method reduces the defective rate of the product and stabilizes its quality.
  • Another embodiment is a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulating layer formed on the display unit, and an organic coating applied to the ends of the barrier layer.
  • the emission characteristics are evaluated by a source meter (Caseley: 2400 series), a semiconductor parameter analyzer (Agilent Technology: E5273A), an optical power meter measuring device (Newport: 1930C), and an optical spectroscope. (Ocean Optics Co., Ltd .: USB2000), spectroradiometer (Topcon Co., Ltd .: SR-3) and streak camera (Hamamatsu Photonics Co., Ltd. C4334 type) were used.
  • Examples 1 to 9, Comparative Examples 1 to 4 Fabrication and evaluation of thin films Compound C1 and Host1 are different vapor deposition sources on a quartz substrate by a vacuum deposition method under the condition that the degree of vacuum is less than 1 ⁇ 10 -3 Pa.
  • using compounds C2 to C9 instead of compounds C1 thin films of Examples 2 to 9 were obtained in order.
  • a thin film of Comparative Example 1 was similarly obtained using Compound A and PPF.
  • each compound used as a light emitting material in Examples and Comparative Examples in the present specification was used after being sublimated and purified before use.
  • photoluminescence was observed in all the thin films.
  • the lifetime of delayed fluorescence ( ⁇ d ) was obtained from the transient attenuation curve of light emission, and the relative value with respect to Comparative Example 1 was calculated with the lifetime of Comparative Example 1 as the key. The results are as shown in the table below. It was confirmed that the delayed fluorescence lifetime ( ⁇ d) of Examples 1 to 9 was short.
  • Example 10 to 14 Comparative Example 2 Fabrication of Organic Electroluminescence Device
  • ITO indium tin oxide
  • HATCN was formed on ITO to a thickness of 10 nm
  • NPD was formed on it to a thickness of 30 nm.
  • TrisPCz was formed on it to a thickness of 10 nm
  • Host1 was further formed on it to a thickness of 5 nm.
  • SF3TRZ Liq (weight ratio) was set to 7: 3. Further, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form a cathode.
  • the organic electroluminescence device of Example 10 was produced.
  • compound C2 compound C3, compound C4, compound C6, and comparative compound A, respectively, instead of compound C1
  • the organic electroluminescence devices of Examples 11 to 14 and Comparative Example 2 were prepared in order.

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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
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  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

L'invention concerne un matériau électroluminescent exceptionnel. Un composé représenté par la formule générale est utilisé en tant que matériau électroluminescent. R est un groupe hétéroaryle lié à un atome d'hydrogène, un atome de deutérium, un groupe aryle, ou un atome de carbone, Ar est un groupe hétéroaryle lié à un groupe aryle ou à un atome de carbone, et D1 et D2 sont des groupes donneurs parmi lesquels au moins l'un est un groupe carbazol-9-yle fusionné à un hétérocycle.
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